Mimetic insect pyrokinin analogs for insect control
Novel pseudopeptide analogs of the insect pyrokinin neuropeptide family which possess biological activity mimicking that of the naturally occurring neuropeptides are disclosed. By addition of a hydrophobic moiety to an active portion of the pyrokinin peptides, analogs are produced which exhibit an overall amphiphilic nature and which are capable of penetrating the insect cuticle while still retaining biological activity. The analogs may be used for insect control by disrupting the reproductive, developmental, and/or digestive processes normally regulated by pryrokinins in insects.
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Claims
1. A compound of the formula
- (a) Cb--(CH.sub.2)--C(O)-- and
- (i) Cb is a carborane, and
- (ii) n is 1, 2, or 3; or
- (b) R.sub.1 --L.sub.n --X.sub.2 --Phe-- and
- (i) R.sub.1 is a hydrophobic moiety selected from the group consisting of aromatic containing amine groups and aromatic containing acyl groups, said hydrophobic moiety being effective to render said compound amphiphilic,
- (ii) n is 0 or 1,
- (iii) L is a spacer which, when R.sub.1 is an aromatic containing acyl group, is selected from the group consisting of non-polar hydrocarbon groups having an amino group and acyl group, and uncharged.alpha.-amino acids, or when R.sub.1 is an aromatic containing amine group, said spacer is a diacyl group, and
- (iv) X.sub.2 is selected from the group consisting of a bond, an amino acid, and a polypeptide group, said polypeptide group comprising all or a portion of a pyrokinin neuropeptide which is naturally contiguous to the C terminal pentapeptide --Phe--X.sub.1 --Pro--Arg--Leu--NH.sub.2, and which said polypeptide group is sufficiently small as to retain the hydrophobicity of said compound introduced by said hydrophobic moiety.
2. The compound of claim 1 wherein R is said Cb--(CH.sub.2).sub.n --C(O)--.
3. The compound of claim 2 wherein said carborane is selected from the group consisting of o-carborane and m-carborane.
4. The compound of claim 1 wherein R is said R.sub.1 --L.sub.n --X.sub.2 --Phe--.
5. The compound of claim 4 wherein X.sub.2 is a bond.
6. The compound of claim 4 wherein X.sub.2 is a polypeptide group having less than or equal to about 7 amino acids.
7. The compound of claim 6 wherein said polypeptide group is --Glu--Gly--Asp--.
8. The compound of claim 4 wherein R.sub.1 is a hydrophobic aromatic containing acyl group, n is 1, and L is selected from the group consisting of non-polar hydrocarbon groups having a free amino group and free acyl group, and uncharged.alpha.-amino acids.
9. The compound of claim 8 wherein R.sub.1 is selected from the group consisting of phenyl alkanoic acyl groups, phenyl alkenoic acyl groups, and phenyl alkynoic acyl groups.
10. The compound of claim 9 wherein R.sub.1 is selected from the group consisting of a 6-phenyl hexanoic acyl group and a 9-phenyl nonanoic acyl group.
11. The compound of claim 8 wherein L is selected from the group consisting of Ala and Gly.
12. The compound of claim 4 wherein R.sub.1 is a hydrophobic aromatic containing acyl group and n is 0.
13. The compound of claim 12 wherein R.sub.1 is selected from the group consisting of phenyl alkanoic acyl groups, phenyl alkenoic acyl groups, and phenyl alkynoic acyl groups.
14. The compound of claim 13 wherein R.sub.1 is selected from the group consisting of a 6-phenyl hexanoic acyl group and a 9-phenyl nonanoic acyl group.
15. A composition comprising the compound of claim 1 and an inert carrier.
16. The composition of claim 15 wherein said carrier is water.
17. A method for controlling insects comprising applying the compound of claim 1 to the locus of said insects.
18. The method of claim 17 wherein said insects are selected from the group consisting of insects of the order Lepidoptera, insects of the order Dictyoptera, insects of the order Diptera, and insects of the order Orthoptera.
19. The method of claim 17 wherein said applying comprises topically applying said compound onto said insects.
20. The method of claim 17 wherein said compound is applied in an amount effective to stimulate pheromone production by said insect.
21. The method of claim 17 wherein said compound is applied in an amount effective to stimulate gut contraction by said insect.
22. The method of claim 17 wherein said compound is applied in an amount effective to stimulate oviduct contraction by said insect.
| 5032576 | July 16, 1991 | Raina et al. |
- Chemical Abstracts 125:159037, "Potent Pheromonotropic/Myotropic Activity of a Carboranyl Pseudopeptide Analog of the Insect Pyrokinin/PBAN Neuropeptide Family", 1996. Chemical Abstracts 123:139491, "Pseudopeptides of the Pyrokinin/PBAN Insect Neuropeptide Family", 1995.
Type: Grant
Filed: Aug 22, 1996
Date of Patent: Aug 18, 1998
Assignee: The United States of America as represented by the Secretary of the Agriculture (Washington, DC)
Inventors: Ronald J. Nachman (Willis, TX), Peter E. A. Teal (Gainesville, FL), Grant Mark Holman (Bryan, TX)
Primary Examiner: Frederick Krass
Attorneys: M. Howard Silverstein, Randall E. Deck, John D. Fado
Application Number: 8/700,915
International Classification: A01N 3718; A61K 3828;
